I am honored and truly humbled to be named Massachusetts Principal of the Year. As we all know, it is a collective effort to create dynamic learning experiences in schools, and I could not accomplish anything without the incredibly talented educators I work with, who equally deserve this award. As I reflect on this recognition, I want to share how a few pivotal moments during my career have shaped who I am as a leader.

The first moment came during my first year as assistant principal. It was the second week of the school year, and it was one of those days when everything was going wrong, and I was the only administrator in the building. In the middle of it all, I was on my way down the hall to help with a student in crisis. I was moving pretty quickly when a teacher coming from the other direction approached me with something in his hand. He informed me that a small piece of plastic had broken off the radiator in his room, and he was very concerned about it. I said, “Thanks. This is pretty low on my priority list, but I will get back to you.” By the time I reached the end of the hall, I knew this had been the wrong thing to say. I could hear my words in my head, and I thought, ‘I just messed up.’

After I finished with the crisis, I returned to my office and wrote an apology and left it in the teacher’s mailbox. Thankfully, the teacher appreciated that I owned my mistake and didn’t hold it against me. What I learned was, in that moment although it wasn’t a priority to me, it was the most important thing to that individual. I had to find a way to acknowledge and validate those feelings, without dismissing them.

Pursuing the Principalship

The second pivotal moment came in March of my third year as an AP. My principal at the time announced that he would be leaving at the end of the year for another district, and I wondered who would be stepping in to take over the school. The other AP had been in the school and in the role longer, but he was pushing me to apply for the job, and I was very unsure. I was only in my third year, and I still was operating under the “fake it ‘til you make it” plan. I didn’t know at the time that that plan never goes away no matter how long you have been doing this job.

I vividly remember calling my best friend Maureen Cohen, who by the way is an incredible superintendent, and we talked through the pros and cons of applying. We made the decision together that I wasn’t going for the job. There was one exception, though, and that was if the superintendent Dr. Brad Jackson called me into his office to talk to me about taking the job. The next day…the phone rang.

What I learned from that experience is that you never really feel ready for the next step, and that often others will believe in you before you might even believe in yourself. Take those opportunities and lean into them because amazing things can happen.

Principal Nicole Bottomley with students at Holliston High School.

My third defining experience happened as I grew into my role as principal. I had just finished reading Timeless Learning: How Imagination, Observation, and Zero-Based Thinking Change Schools by Pam Moran, Ira Socol, and Chad Ratfliff. A chapter in the book described an amazing three-level tree house that Pam had said yes to building in the cafeteria. The whole book is about leading from a place of yes, a philosophy I share and one that really resonated with me.

At the time, a senior in my school was working on his original production of a film that he had written and was now producing for a senior project. He asked to meet with me to discuss his final scene. He requested to film the final scene on the school’s roof. I am not sure whether it was his impassioned speech or the tree house in the book, but I said yes. I remember the shock on his face and him saying, “Wow! My mom said you would never say ‘yes.’” At that point, I wondered, did I just make a mistake?

Now, it is a much better story when I leave out the fact that the roof was only one level up, and the ground was soft grass below it, so really how bad could it be? I also wanted to keep my job, so I did make sure we were as safe as possible. The student filmed his last scene on the roof, presented his video to an audience, graduated, and went off to Emerson College in Boston for film study.

He later returned to let me know how much it meant to him that he could bring his dream to life. This moment solidified for me the need to lead from a place of yes, which I try to live by as much as possible.

The reality is we may never know the influence we will have on others. We have an amazing job as leaders in schools. We have the immense privilege of leading buildings of students and educators who are full of possibility and who dream of the future. The energy that exists in a school cannot be matched anywhere else. Our job is truly the best.

Learn more about NASSP’s Principal of the Year program.

About the Author

Nicole Bottomley is the principal of King Philip Regional High School in Wrentham, MA, and the former principal of Holliston High School in Holliston, MA. She is the 2023 Massachusetts Principal of the Year. This post draws from remarks she gave last month at the Massachusetts School Administrators’ Association Summer Institute.

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